Allyl alcohol, a well-known monomer, is available commercially from isomerization of propylene oxide. Ethylenic polymerization of allylic alcohols with other olefins is a potential route to polymers that have a high concentration of primary hydroxyl groups. Such copolymers are potentially valuable polymers intermediates because they will cure rapidly with isocyanates, anhydrides, and melamine resins to give useful thermoset articles.
Few allylic alcohol copolymers have actually become commercially important. Poly(allyl alcohol), for example, is not widely used in spite of its high concentration of primary hydroxyl groups because of its poor solubility in most common organic solvents. Copolymers of allyl alcohol and typical vinyl monomers such as styrene are known, but because allyl alcohol reacts much more slowly than vinyl monomers, a large excess of allyl alcohol is needed in the copolymerization to get a desirable hydroxyl group content.
Allyl ester polymers are known, but because allyl esters polymerize slowly with even high levels of free-radical initiators to give polymers of only low molecular weight, few allyl esters have any industrial use for polymers and copolymers (see S. R. Sandler and W. Karo, Polymer Syntheses, Vol. III (1980), Chapter 8, "Polymerization of Allyl Esters," pp. 248-294, at page 263).
Sackmann et al. (U.S. Pat. No. 3,876,588) disclose a terpolymer of allyl alcohol, allyl acetate, and maleic anhydride, but do not describe terpolymers of allylic alcohols, allyl esters, and vinyl monomers
New hydroxy-functional allyl terpolymers are needed. Particularly valuable terpolymers would be easy to prepare and would have a high concentration of hydroxyl groups. Preferably, the terpolymers would be soluble in common organic solvents to enable easy formulation into polyurethanes, polyesters, melamines, alkyd coatings, uralkyds, and other thermoset polymers.